


See You In the Morning (Not)

by maria_j_harper



Category: Homestuck
Genre: Alternate Universe - Prostitution, Anal Sex, M/M, Sexual Content
Language: English
Status: Completed
Published: 2014-08-28
Updated: 2014-08-28
Packaged: 2018-02-15 04:12:25
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,806
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2215362
Author URL: https://archiveofourown.org/users/maria_j_harper/pseuds/maria_j_harper
Summary: <blockquote class="userstuff">
              <p>"You don't pay a prostitute for sex, you pay <s>her</s> him to leave afterwards." --Daschiell Hammett</p><p>Or: In which Jake is a prostitute, and Dirk has commitment issues.</p>
            </blockquote>





	See You In the Morning (Not)

Your name is Dirk Strider, and you know exactly who is knocking on your door. Well that's not strictly true, you don't know his name, but you know why he's here. You get up and answer the door. "Hey. Come on in."  
The dark haired man looks embarrassed as he walks into your apartment. He must be new to the agency or something. Or maybe the Shy Boy is his thing? If it is, it's working for him. He's very good looking, only to be expected, you'd chosen his employers over any other dial-a-bang for a reason. They were a call-girl/boy agency with class. Still, the juxtaposition of his sculpted muscles, tan skin and vibrant green eyes against his shy uncertainty was kind of adorable.  
You hold out your hand. "Call me Dirk," you say.  
"Jake," he says in return.  
"Nice to meet you Jake. Shall we get started?"  
"Right, um..." He reaches down to fumble with the fly of his pants. You step closer and take his hands in yours.  
"Where's the fire Jake? Foreplay's half the fun." You kiss his lips tenderly and pretend that you love him. just for tonight, you can pretend that you love him.  
"S-sorry, I suppose I'm just a tad flustered and nervous because you're sort of my first male client. Not that I don't- I'm bisexual, I- Anyways, up to now I've mostly worked baccholoett parties and stuff," Jake explains, looking away with a blush.  
You chuckle slightly. "C'mon, let's take this to the bedroom, shall we?" He nods and lets you lead him to your room. "Sorry 'bout the mess," you add, a bit embarrassed by your clutter.  
"Don't worry about it... babe?"  
His uncertainty really is adorable, but you like it even better when he seems to gain a little more nerve, enough to kiss you again. Your hands go for the buttons on his shirt, and he helps you open it so that it parts to reveal hard muscles and not an ounce of fat on him. You push his shirt off and as it slides from his arms to the floor you notice a thin white scar on his shoulder. "What's this?"  
"Just something I got working. You may not believe this, but I'm normally the one chosen by the more err... adventurous clientele. Adventurous is sort of my thing."  
You laugh. "Well I guess it makes sense why they'd send you to me then, I'm afraid I may have developed a bit of a reputation." You pull your shirt up and over your head. You watch Jake as his eyes trace over you. You have  
more scars than he does, and a tattoo on your shoulder of a character from your bro's famous comic. You kiss him again, one hand on his back to pull him close, the other exploring his upper body. Brushing over his chest to caress his abs and then finally rest on his waist. He kisses you back, and his hands begin doing a little exploring of their own, tentatively at first, then with more confidence. You breathe him in.  
He surprises you when he reaches down toward your belt and unbuckles it, pulling it open so that your pants hang loose. "Thought you were nervous."  
"Yes, well, I'm feeling better now. Besides, I do want to give you what you paid for."  
"Jake, I didn't pay you for sex." You look him in the eye. You can't believe you're the one telling him this.  
"You... didn't?"  
"No. I can walk into pretty much any gay bar in town and find someone willing to come home and have sex with me. What I'm paying you for is to leave after we're done. Someone I brought home from a bar? Maybe they'd be cool with a one-night stand but maybe not. With people from the agency like you though, you know not to expect an emotional connection. It's a business transaction, nothing more. Long story short, I have some commitment issues." You smirk, as you watch confusion and pity chase each other around on Jake's open face. "That doesn't mean we can't enjoy ourselves though, right?"  
"Right." He kisses your mouth, and you probe between his lips with your tongue. His tongue meets yours, and you feel your dick starting to harden in excitement. He breaks away from the kiss and kisses your neck. His hands find places to rest, one on your lower back and one on your pectoral. Then he moves downward, leaving a trail of small kisses right down the middle of your chest between your rows of abs. His tan complexion makes a contrast with your rather pale skin, you notice. It looks nice, but not nearly as nice as it feels. He slowly moves to a kneeling position in front of you and he pulls down your already sagging pants. Your boner is fully erect now, and your tight briefs do nothing to hide this fact. Jake seems a bit intimidated, and you remember that he probably hasn't played with any dick that wasn't his own. Still, when he reaches out and touches it through the cloth, you moan in pleasure.  
You let out a rather uncool gasp when he wraps his fingers over the bulge in your underwear and gives it a stroke. Your loins feel tight with building tension, and you quickly remove your briefs, stepping out of them along with the pants that had still been pooled around your ankles. Jake hesitates, but only briefly, and then his fingers gently explore your length from tip to base. "I don't know how we are going to fit this inside of me," he says.  
"Would you like me to help you figure it out?"  
"No! I mean... I know what to do. I was trained for this you know. I'm just..."  
"Realizing the difference between text books and porn tapes and real life, yeah, I know. I had a first time too." You grab his arm and lift him up from his knees, guiding him to the bed. You start to reach to pull his pants off of him, but so does he.  
"Let me do it," he says, so you do. He removes his pants and boxers both, leaving you both naked. He has an erection of his own, and you reach down to rub it over with your hand. He lets out a moaning sigh. "Dirk." He whispers your name.  
You take him by the shoulders and sit him down on the bed. You then remember that you left the condoms and lube in your pants pocket. Stupid really. "Don't go anywhere," you tell him. You go and get your supplies from your pocket and come back. You put the lube on the bedside table so you can put on your condom. You then take the second one over to Jake. He reaches for it, but you pull it away from his grasp. "Let me do it."  
You reach for the base of his dick, and stroke it slowly upward. He groans, and you feel his eyes on you as you unroll the condom down over his length. You plant a kiss on the side of his dick, and then reach for the lube. You squeeze some out over your fingers, and you make eye contact with him as you reach down to slick his ass with it. He makes a slightly uncomfortable face, not that you can blame him. This, you've always found, is one of the grosser parts of anal sex, even when you're used to it. You kiss him, and are comforted by the fact that he kisses you back.  
"This is probably going to feel a bit weird," you warn him. You press your index finger into his ass, and you see him wince. You use your other hand to caress his dick, and his look of discomfort turns to one of pleasure. You add in your middle finger slowly, widening his opening and preparing it for you to enter. You continue to stroke Jake's dick, and he makes a small whimper as pain and pleasure mingle. You push you fingers deeper, and your middle finger finds his sweet spot. His breath hitches and he gasps in unexpected pleasure. You withdraw your fingers and slick your dick over with lube.  
You press into Jake slowly, lying him back on the bed as you push forward. He moans, then gasps again, and you're moaning too. You begin pumping, creating a slow rhythm which gradually gained speed as the tension in your loins built, until it became an almost unbearable pressure. You're panting, and so is he, and you're both so close.  
"Dirk!" He moans your name. "Oh Dirk!"  
"Jake." It feels a bit strange, you don't usually say anyone's name during sex, but you want to say his. You say it again, and suddenly you can't hold back anymore. You cry out as the orgasm washes over you, a great release. You pump Jake's dick rapidly with your hand, and he cums with you still inside of him.  
You pull out and collapse on the bed next to him, arm draped over his chest. "So... was it as scary as you though it would be?"  
"To be honest... yes, but I'm glad that I got over that fear Dirk."  
"Good. Now... I'm gonna go get cleaned up." You get up, and pick up your discarded clothes on the way to the bathroom. You toss them in the laundry hamper. In the bathroom you peel off the used condom, use a washcloth to clean your genitals of any residual cum, and put on a clean pair of underwear. You come back into the room and gesture Jake to the bathroom. "You wanna clean up too?"  
He nods and disappears behind the bathroom door. You sit on the bed and wait for him to come back out. After the warmth of his body against yours, the bed feels cold and you shiver slightly. He comes back out and immediately starts picking up his clothes. He puts his underwear back on too, and starts to button up his shirt. He puts the first button in the second hole, and has to start over again.  
"Got someplace else to be Jake?"  
He freezes. "Well... no, but I was under the impression I was being paid to not overstay my welcome. That is what you told me Mr. Strider."  
His shift from casually calling out your name to this stiff formal address should not hurt this much. Your body still remembers exactly where he touched you, and even though sexually you are completely spent, another kind of longing, just as strong, compells you to say "Stay."  
"What?"  
"Stay with me a while. Please?"  
He smiles softly, and sits beside you on your bed.


End file.
